(S)-N-((S)-1-phenylethyl)-5-oxopyrrolidine-2-carboxamide | 261951-62-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-((S)-1-phenylethyl)-5-oxopyrrolidine-2-carboxamide
• 英文别名: 5-oxo-pyrrolidine-2-carboxylic acid (1-phenylethyl)amide；N-[(S)-1-phenylethyl]-L-pyroglutamide；(2S)-5-Oxo-N-[(1S)-1-phenylethyl]-2-pyrrolidinecarboxamide；(2S)-5-oxo-N-[(1S)-1-phenylethyl]pyrrolidine-2-carboxamide
• CAS: 261951-62-6
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: JVGNGXYORDYMPR-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-((S)-1-phenylethyl)-5-oxopyrrolidine-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以49.2%的产率得到(S)-1-phenylethyl((S)-pyrrolidin-2-ylmethyl)amine
  参考文献：
  名称：

  Synthesis and characterization of chiral 1,2-diamines from 5-oxo-pyrrolidine-(S)-2-carboxylic acid

  摘要：

  Unsymmetrical chiral secondary vicinal diamines were synthesized by applying a modified three-step reaction. The key step in this sequence is a primary amine mediated ring opening reaction of a diastereomeric oxazolidinone derivative. A possible mechanism for this step is described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.07.012
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 L-焦谷氨酸甲酯 生成 (S)-N-((S)-1-phenylethyl)-5-oxopyrrolidine-2-carboxamide
  参考文献：
  名称：

  高度功能化支架的发现：吡咯并咪唑二酮类作为P2X7受体拮抗剂

  摘要：

  通过1-吡咯戊酰胺衍生物与Bredereck试剂之间的环加成反应获得了广泛的吡咯并咪唑二酮类化合物，它们是新的高度官能化的双环杂环。随后的吡咯并咪唑二酮的甲醇分解作用提供了P2X7受体拮抗剂，并保留了最初的立体构型，在治疗炎症和神经系统疾病方面具有潜在的应用前景。因此，我们开发了一种新的内酰胺氮游离烯胺酮的合成方法，这是目前文献中引用的最简单的方法来获得这些化合物。

  DOI：

  10.1016/j.tet.2017.07.036

文献信息

• On the discovery of new potent human farnesyltransferase inhibitors: emerging pyroglutamic derivatives
  作者：Germain Homerin、Emmanuelle Lipka、Benoît Rigo、Amaury Farce、Joëlle Dubois、Alina Ghinet

  DOI：10.1039/c7ob01489a

  日期：——

  context of lack of emergence of innovative human farnesyltransferase inhibitors families, and given all new therapeutic perspectives that open up for such molecules in rare diseases (e.g. Hutchinson–Gilford progeria syndrome), and in delta hepatitis, cardiovascular or neuroinflammatory diseases, we have just discovered a new series of powerful inhibitors. These molecules are pyroglutamic acid derivatives

  在目前缺乏创新的人类法呢基转移酶抑制剂家族的背景下，并鉴于所有新的治疗方法都为罕见病（例如Hutchinson-Gilford早衰综合症）以及三角洲肝炎，心血管或神经炎性疾病中的此类分子打开了大门，刚刚发现了一系列功能强大的抑制剂。这些分子是焦谷氨酸衍生物，并在体外通过人法呢基转移酶进行了评估，然后在计算机上对该蛋白质的活性位点进行了建模。焦谷氨酸循环的三个主要点在位置5经历了焦磷酸谷酰胺的化学调制（化合物7a–h），吡咯并咪唑二酮类型的受限双环类似物（化合物1a–h），位置3的调制（化合物2–5和8），并允许该领域的第一个SAR。当前工作中的五种衍生物的IC 50值在小纳摩尔范围内（2-5 nM）。这些新的先导化合物为下一代法呢基转移酶抑制剂开辟了道路。
• Five- and Six-Membered Ring Opening of Pyroglutamic Diketopiperazine
  作者：Dennis A. Parrish、Lon J. Mathias

  DOI：10.1021/jo0160928

  日期：2002.3.1

  A variety of ring-opening reactions of pyroglutamic diketopiperazine at both the five-membered and six-membered rings is described. Mild, basic conditions facilitate nucleophilic attack by amines at the diketopiperazine carbonyls giving pyroglutamides in excellent yield. Reaction with nucleophiles under acidic conditions give bis-glutamate derivatives of 2,5-diketopiperazine (DKP). These reactions

  描述了焦谷氨酸二酮哌嗪在五元和六元环上的各种开环反应。温和的碱性条件促进胺在二酮哌嗪羰基上的亲核攻击，从而以优异的收率得到焦谷氨酰胺。在酸性条件下与亲核试剂反应，可生成2，5-二酮哌嗪（DKP）的双谷氨酸衍生物。这些反应为商业焦谷氨酸中的焦谷酰胺和对称二酮哌嗪提供了简单的两步序列，并控制了反应条件，催化剂和亲核试剂对产物的控制。
• Synthesis and X-ray crystal structure of dichloro[S-1-phenyl-N-(S-pyrrolidin-2-ylmethyl)ethanamine]zinc(II) and its catalytic application to rac-lactide polymerization
  作者：Saira Nayab、Hyosun Lee、Jong Hwa Jeong

  DOI：10.1016/j.poly.2010.11.002

  日期：2011.2

  New dichloro zinc(II) complex ligated by the homochiral bidentate ligand S-1-phenyl-N-(S-pyrrolidin-2-ylmethyl)ethanamine (PPMA) was synthesized and characterized by X-ray crystallography. The geometry of the (PPMA)ZnCl2 is a distorted tetrahedron comprising of zinc metal as a center linked with two N atoms of the PPMA in a bidentate coordination mode along with two chloro ligands. The catalytic capacity of the complex was evaluated in ring opening polymerization (ROP) of rac-lactide. The active catalyst species was generated in situ by treating MeLi to complex (PPMA)ZnCl2. The dimethyl derivative of the (PPMA)ZnCl2 showed highly activity in ROP of rac-lactide and gave preference to heterotactic polylactide. (C) 2010 Elsevier Ltd. All rights reserved.
• Discovery of highly functionalized scaffolds: Pyrroloimidazolediones as P2X7 receptor antagonists
  作者：Germain Homerin、Emmanuelle Lipka、Benoît Rigo、Régis Millet、Xavier Dezitter、Christophe Furman、Alina Ghinet

  DOI：10.1016/j.tet.2017.07.036

  日期：2017.8

  A broad range of pyrroloimidazolediones, new highly functionalized bicyclic heterocycles, was obtained by a cycloaddition reaction between l-pyroglutamide derivatives and Bredereck's reagent. Methanolysis of subsequent pyrroloimidazolediones provided antagonists of P2X7 receptor, with retention of initial stereoconfiguration, with potential applications in the treatment of inflammatory and neurological

  通过1-吡咯戊酰胺衍生物与Bredereck试剂之间的环加成反应获得了广泛的吡咯并咪唑二酮类化合物，它们是新的高度官能化的双环杂环。随后的吡咯并咪唑二酮的甲醇分解作用提供了P2X7受体拮抗剂，并保留了最初的立体构型，在治疗炎症和神经系统疾病方面具有潜在的应用前景。因此，我们开发了一种新的内酰胺氮游离烯胺酮的合成方法，这是目前文献中引用的最简单的方法来获得这些化合物。
• Synthesis and characterization of chiral 1,2-diamines from 5-oxo-pyrrolidine-(S)-2-carboxylic acid
  作者：Uwe Köhn、Andrea Schramm、Florian Kloß、Helmar Görls、Evelyn Arnold、Ernst Anders

  DOI：10.1016/j.tetasy.2007.07.012

  日期：2007.7

  Unsymmetrical chiral secondary vicinal diamines were synthesized by applying a modified three-step reaction. The key step in this sequence is a primary amine mediated ring opening reaction of a diastereomeric oxazolidinone derivative. A possible mechanism for this step is described. (c) 2007 Elsevier Ltd. All rights reserved.